


Be My Baby Tonight

by acklesbbykate



Series: Inspired By Songs [9]
Category: Supernatural
Genre: Based on a song, Castiel and Dean Winchester are Cute, Dean and Cas Ship Sam Winchester/Jessica Moore, Established Castiel/Dean Winchester, F/M, Fluff, Grand Gesture, Jessica Likes Sam, Jessica Moore and Sam Winchester are Cute, M/M, Sam Likes Jessica, Sam Winchester Ships Castiel/Dean Winchester, Sam Winchester Sings, Sam-Centric, Sassy Jessica
Language: English
Status: Completed
Published: 2017-12-18
Updated: 2017-12-18
Packaged: 2019-02-16 10:20:39
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,096
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13052043
Author URL: https://archiveofourown.org/users/acklesbbykate/pseuds/acklesbbykate
Summary: ~"Jess is amazing and radiant and one of a kind. She’s strong and independent. She doesn’t go for the heart eyes and wolf whistles. She needs a grand gesture. What do I do to even get her attention?” Dean tapped his fingers on the table as he thought, then he looked up at the drunk young woman singing off-key about single ladies on the karaoke stage. He grinned as he pointed up there and raised an eyebrow at Sam. Sam glanced up there then quickly back at Dean, a huge grin on his face, puppy eyes lit up bright.~Sam has been pining for Jess for months, but he just doesn't know how to sweep her off her feet. Will a little John Michael Montgomery do the trick?What can I do to prove to you I'm a layin' it on the lineI'll even get down on my knees just to beg you one more time





	Be My Baby Tonight

**Author's Note:**

> Based on Be My Baby Tonight by John Michael Montgomery  
> [Lyric Video](https://www.youtube.com/watch?v=10hxo4F1ZyA)

Sam watched Jess across the room where she was taking down orders from a table of rowdy frat boys. All of them were making ‘heart-eyes’ at her and one even wolf-whistled. She just laughed it off and took it in stride like always.

“Samantha, you’re making me sick with the love-struck puppy eyes. Just go ask the girl out already.” Dean shook his head and leaned back in his chair, wrapping an arm around his fiancée’s shoulders. Cas looked up at him with a raised eyebrow and quipped, “I seem to remember someone else with love struck puppy eyes, Dean.” Dean smiled adoringly down at Cas and sighed softly.

Sam was watching his older brother and soon to be brother-in-law with a small smile, happy that they have each other. “Y’all are cute, and in the words of Charlie, ‘I ship it’, but you guys… Jess is, she’s amazing and radiant and one of a kind. She’s strong and independent. She doesn’t go for the heart eyes and wolf whistles. She needs a grand gesture. What do I do to even get her attention? You have to help me.”

Dean tapped his fingers on the table as he thought, then he looked up at the drunk young woman singing off-key about single ladies on the karaoke stage. He grinned as he pointed up there and raised an eyebrow at Sam.

Sam glanced up there then quickly back at Dean, a huge grin on his face, puppy eyes lit up bright. “Dean, yes, that’s a great idea! She likes country music… what should I sing?”

The three men deliberated on their options for a little while before deciding the best way to choose was to look through the options in their book.

“You and Cas go look through there and pick the song. He’s better with the romance crap anyway.” He smirked at the rolling eyes of his raven-haired fiancée. “I’ll go see what time Jess’s shift ends and sweet talk her into staying for a bit after. We all know I’m the charming one around here.” He ducked at the napkin Sam threw at him and walked away chuckling.

Sam and Cas made their way up to the DJ booth at the side of the stage and flipped through to the Country section. They looked at the songs, talking about which ones Sam knew and which one’s weren’t good choices. When they stumbled across the John Michael Montgomery classic, Sam jammed his finger at it excitedly.

“This one! She’ll love it! It’s perfect!” He looked across the bar to see his brother, true to form, smoothly charming Jess into staying. They waited at the booth until Dean came over and confirmed that Jess was about to clock out and would meet them back at their table. Sam got everything squared away with the DJ, who was happy to help him woo the sweet blonde waitress, then they sat back down. 

“Okay, Casanova. When she gets here, you go on up to the stage and Cas and I will get her front and center at the stage. You ready to win your woman?” Dean grinned at his baby brother’s enthusiastic nod.

When Jess pulled out the fourth chair at the table and sat down, she immediately smiled over at Sam. “Hi, Sam.”

He grinned at her. “Hey, Jess. Excuse me.” He rose and walked towards the DJ booth.

Jess looked over at Dean questioningly. Dean wiggled his eyebrows and said, “C’mon, little lady.” He and Cas stood, both offering an arm to her. When she laughed and put one hand in each man’s arm, they walked her towards the stage.

“Dean, what’s going…”

“Just relax and enjoy the show, little lady,” Dean said with a southern twang. Cas pulled a chair away from an empty table right in front of center stage where the mic was set up. Jess gingerly sat down, and the boys made their way back to the table to watch.

As Sam made his way up to the mic, the upbeat drum and guitar intro began. He smoothly grabbed the mic, grinned down at Jess, and started singing.

_“I know you've heard that worn out line about love at first sight_  
_Well, I never knew those words were true till you walked in tonight”_

He finished the verse then sat down on the edge of the stage to sing the chorus directly to Jess, who had a hand over her smiling mouth.

_“Could ya, would ya, ain't ya gonna, if I asked you would ya wanna be my baby tonight_  
_Take a chance, slow dance, make a little romance-Honey, it'll be alright_  
_Girl you got me wishin' we were huggin' and a kissin' and a holdin' each other tight_  
_So, could ya, would ya, ain't ya gonna, if I asked you would ya wanna be my baby tonight”_

He swayed along with the music, patting his heart, pointing out at Jess, and really laying it on thick as he sang the next verse and chorus. Then he jumped off the edge of the stage as the guitar solo picked up and grabbed Jess’s hand. He pulled her to her feet and two stepped a bit with her in front of the stage, finally spinning her around a few times and dropping her back into her chair.

When he hopped back up onto the stage, he put the mic back in the stand and belted out the last chorus. Then he dropped to his knees at the edge of the stage and sang only to Jess.

_“Yeah, could ya, would ya, ain't ya gonna_  
_If I asked you would ya wanna_  
_Be my baby tonight”_

Jess, along with the rest of the bar, applauded and whistled. Then she stood and walked up to the stage, crooking her finger at Sam to beckon his face closer. When he jumped off the stage and dipped his head, she grabbed him around the back of his neck and jammed their lips together.

Dean let out a war-whoop and Cas simply smiled and clapped, then they both made their way up to where Sam, love struck puppy eyes firmly in place, was watching Jess. Dean clapped Sam on the back and Cas gave him a thumbs-up.

“So, Samsquatch, what are your plans for the rest of the night?”

Jess took Sam’s hand and smirked at Dean. “I’ve been waiting on him to ask me out for months. Don’t wait up.”

Dean and Cas grinned at each other and watched as the feisty blonde dragged Sam out the door.

**Author's Note:**

> This song came on and my mind just ran away with it. *has no regrets* :D Hope y'all enjoyed! Kudos/Comment <3


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